Adenosine-derived inhibitors of 78 kDa glucose regulated protein (Grp78) ATPase: Insights into isoform selectivity

Journal of Medicinal Chemistry

Volumn 54, Issue 12, 2011, Pages 4034-4041

  MacIas, Alba T ^a   Williamson, Douglas S ^a   Allen, Nicola ^a   Borgognoni, Jenifer ^a   Clay, Alexandra ^a   Daniels, Zoe ^a   Dokurno, Pawel ^a   Drysdale, Martin J ^a   Francis, Geraint L ^a   Graham, Christopher J ^a   Howes, Rob ^a   Matassova, Natalia ^a   Murray, James B ^a   Parsons, Rachel ^a   Shaw, Terry ^a   Surgenor, Allan E ^a   Terry, Lindsey ^a   Wang, Yikang ^a   Wood, Mike ^a   Massey, Andrew J ^a  

^a Vernalis PLC   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (6 AMINO 8 METHYLAMINOPURIN 9 YL) 5 (PYRIDIN 3 YLMETHOXYMETHYL)TETRAHYDROFURAN 3,4 DIOL; 2 (6 AMINO 8 METHYLAMINOPURIN 9 YL) 5 BENZYLOXYMETHYLTETRAHYDROFURAN 3,4 DIOL; 2 (6 AMINO 8 METHYLAMINOPURIN 9 YL) 5 CYCLOHEXYLMETHOXYMETHYLTETRAHYDROFURAN 3,4 DIOL; 2 [5 (6 AMINO 8 METHYLAMINOPURIN 9 YL) 3,4 DIHYDROXYTETRAHYDROFURAN 2 YLMETHOXY]ACETAMIDE; 2 [6 AMINO 8 [(QUINOLIN 2 YLMETHYL)AMINO]PURIN 9 YL] 5 HYDROXYMETHYLTETRAHYDROFURAN 3,4 DIOL; ADENOSINE; ADENOSINE TRIPHOSPHATASE INHIBITOR; ADENOSINE TRIPHOSPHATE; ADENYLYLIMIDODIPHOSPHATE; BAG 1 PROTEIN; GLUCOSE REGULATED PROTEIN 78; HEAT SHOCK COGNATE PROTEIN 70; HEAT SHOCK PROTEIN 70; ISOPROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNOVIAL FLUID LEVEL; ISOTHERMAL TITRATION CALORIMETRY; PROTEIN STRUCTURE; SURFACE PLASMON RESONANCE;

ADENOSINE TRIPHOSPHATASES; ADENOSINE TRIPHOSPHATE; ADENYLYL IMIDODIPHOSPHATE; BINDING SITES; CALORIMETRY; CRYSTALLOGRAPHY, X-RAY; FURANS; HEAT-SHOCK PROTEINS; HSC70 HEAT-SHOCK PROTEINS; HSP70 HEAT-SHOCK PROTEINS; LIGANDS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN ISOFORMS; PURINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PLASMON RESONANCE; THERMODYNAMICS;

EID: 79959476814     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101625x     Document Type: Article

References (37)

1. Mayer, M. P.; Bukau, B. Hsp70 chaperones: cellular functions and molecular mechanism Cell. Mol. Life Sci. 2005, 62, 670-684
2. Bukau, B.; Weissman, J.; Horwich, A. Molecular chaperones and protein quality control Cell 2006, 125, 443-451
3. Jiang, J.; Prasad, K.; Lafer, E. M.; Sousa, R. Structural basis of interdomain communication in the Hsc70 chaperone Mol. Cell 2005, 20, 513-524 (Pubitemid 41668637)
4. Vogel, M.; Bukau, B.; Mayer, M. P. Allosteric regulation of Hsp70 chaperones by a proline switch Mol. Cell 2006, 21, 359-367 (Pubitemid 43163531)
5. Amor-Mahjoub, M.; Gomez-Vrielyunck, N.; Suppini, J. P.; Fouchaq, B.; Benarouj, N.; Ladjimi, M. Involvement of the interdomain hydrophobic linker and the C-terminal helices in self-association of the molecular chaperone HSC70 Arch. Inst. Pasteur Tunis 2006, 83, 53-62
6. Sondermann, H.; Scheufler, C.; Schneider, C.; Hohfeld, J.; Hartl, F. U.; Moarefi, I. Structure of a Bag/Hsc70 complex: convergent functional evolution of Hsp70 nucleotide exchange factors Science 2001, 291, 1553-1557 (Pubitemid 32179223)
7. Haas, I. G. BiP (GRP78), an essential hsp70 resident protein in the endoplasmic reticulum Experientia 1994, 50, 1012-1020
8. Lee, A. S. The ER chaperone and signaling regulator GRP78/BiP as a monitor of endoplasmic reticulum stress Methods 2005, 35, 373-381 (Pubitemid 40445371)
9. Dong, D.; Ni, M.; Li, J.; Xiong, S.; Ye, W.; Virrey, J. J.; Mao, C.; Ye, R.; Wang, M.; Pen, L.; Dubeau, L.; Groshen, S.; Hofman, F. M.; Lee, A. S. Critical role of the stress chaperone GRP78/BiP in tumor proliferation, survival, and tumor angiogenesis in transgene-induced mammary tumor development Cancer Res. 2008, 68, 498-505 (Pubitemid 351380077)
10. Li, J.; Lee, A. S. Stress induction of GRP78/BiP and its role in cancer Curr. Mol. Med. 2006, 6, 45-54
11. Misra, U. K.; Gonzalez-Gronow, M.; Gawdi, G.; Pizzo, S. V. The role of MTJ-1 in cell surface translocation of GRP78, a receptor for alpha 2-macroglobulin-dependent signaling J. Immunol. 2005, 174, 2092-2097 (Pubitemid 40223952)
12. Delpino, A.; Castelli, M. The 78 kDa glucose-regulated protein (GRP78/BIP) is expressed on the cell membrane, is released into cell culture medium and is also present in human peripheral circulation Biosci. Rep. 2002, 22, 407-420 (Pubitemid 36020682)
13. Kelber, J. A.; Panopoulos, A. D.; Shani, G.; Booker, E. C.; Belmonte, J. C.; Vale, W. W.; Gray, P. C. Blockade of Cripto binding to cell surface GRP78 inhibits oncogenic Cripto signaling via MAPK/PI3K and Smad2/3 pathways Oncogene 2009, 28, 2324-2336
14. Misra, U. K.; Deedwania, R.; Pizzo, S. V. Activation and cross-talk between Akt, NF-kappaB, and unfolded protein response signaling in 1-LN prostate cancer cells consequent to ligation of cell surface-associated GRP78 J. Biol. Chem. 2006, 281, 13694-13707 (Pubitemid 43855285)
15. Ranganathan, A. C.; Zhang, L.; Adam, A. P.; Aguirre-Ghiso, J. A. Functional coupling of p38-induced up-regulation of BiP and activation of RNA-dependent protein kinase-like endoplasmic reticulum kinase to drug resistance of dormant carcinoma cells Cancer Res. 2006, 66, 1702-1711 (Pubitemid 43259955)
16. Reddy, R. K.; Mao, C.; Baumeister, P.; Austin, R. C.; Kaufman, R. J.; Lee, A. S. Endoplasmic reticulum chaperone protein GRP78 protects cells from apoptosis induced by topoisomerase inhibitors: role of ATP binding site in suppression of caspase-7 activation J. Biol. Chem. 2003, 278, 20915-20924 (Pubitemid 36806399)
17. Lee, A. S. GRP78 induction in cancer: therapeutic and prognostic implications Cancer Res. 2007, 67, 3496-3499 (Pubitemid 46762126)
18. Park, H. R.; Furihata, K.; Hayakawa, Y.; Shin-Ya, K. Versipelostatin, a novel GRP78/Bip molecular chaperone down-regulator of microbial origin Tetrahedron Lett. 2010, 43, 6941-6945
19. Yoneda, Y.; Steiniger, S. C.; Capkova, K.; Mee, J. M.; Liu, Y.; Kaufmann, G. F.; Janda, K. D. A cell-penetrating peptidic GRP78 ligand for tumor cell-specific prodrug therapy Bioorg. Med. Chem. Lett. 2008, 18, 1632-1636 (Pubitemid 351318249)
20. Kim, Y.; Lillo, A. M.; Steiniger, S. C.; Liu, Y.; Ballatore, C.; Anichini, A.; Mortarini, R.; Kaufmann, G. F.; Zhou, B.; Felding-Habermann, B.; Janda, K. D. Targeting heat shock proteins on cancer cells: selection, characterization, and cell-penetrating properties of a peptidic GRP78 ligand Biochemistry 2006, 45, 9434-9444 (Pubitemid 44223248)
21. Misra, U. K.; Mowery, Y.; Kaczowka, S.; Pizzo, S. V. Ligation of cancer cell surface GRP78 with antibodies directed against its COOH-terminal domain up-regulates p53 activity and promotes apoptosis Mol. Cancer Ther 2009, 8, 1350-1362
22. Williamson, D. S.; Borgognoni, J.; Clay, A.; Daniels, Z.; Dokurno, P.; Drysdale, M. J.; Foloppe, N.; Francis, G. L.; Graham, C. J.; Howes, R.; Macias, A. T.; Murray, J. B.; Parsons, R.; Shaw, T.; Surgenor, A. E.; Terry, L.; Wang, Y.; Wood, M.; Massey, A. J. Novel adenosine-derived inhibitors of 70 kDa heat shock protein, discovered through structure-based design J. Med. Chem. 2009, 52, 1510-1513
23. Massey, A. J.; Williamson, D. S.; Browne, H.; Murray, J. B.; Dokurno, P.; Shaw, T.; Macias, A. T.; Daniels, Z.; Geoffroy, S.; Dopson, M.; Lavan, P.; Matassova, N.; Francis, G. L.; Graham, C. J.; Parsons, R.; Wang, Y.; Padfield, A.; Comer, M.; Drysdale, M. J.; Wood, M. A novel, small molecule inhibitor of Hsc70/Hsp70 potentiates Hsp90 inhibitor induced apoptosis in HCT116 colon carcinoma cells Cancer Chemother. Pharmacol. 2010, 66, 535-545
24. Holmes, R. E.; Robins, R. K. Purine Nucleosides. IX. The synthesis of 9-beta- d -ribofuranosyl uric acid and other related 8-substituted purine ribonucleosides J. Am. Chem. Soc. 1965, 87, 1772-1776
25. Long, R. A.; Robinds, R. K.; Townsend, L. B. Purine nucleosides. XV. The synthesis of 8-aminoand 8-substituted aminopurine nucleosides J. Org. Chem. 1967, 32, 2751-2756
26. Ikehara, M.; Tada, H.; Muneyama, K.; Kaneko, M. Synthesis of purine cyclonucleoside having an 8,2′- O -anhydro linkage J. Am. Chem. Soc. 1966, 88, 3165-3167
27. Sasaki, T.; Minamoto, K.; Fujiki, Y. Systematic synthesis of purine 8,5′-imino and substituted imino cyclonucleosides Chem. Lett. 1983, 7, 1017-1020
28. Chattopadhyaya, J. B.; Reese, C. B. Reaction between 8-bromoadenosine and amines. Chemistry of 8-hydrazinoadenosine Synthesis 1977, 10, 725-726
29. Huang, X. Fluorescence polarization competition assay: the range of resolvable inhibitor potency is limited by the affinity of the fluorescent ligand J. Biomol. Screening 2003, 8, 34-38
30. i values for inhibitors of enzyme activity and ligand binding Nucleic Acids Res. 2009, 37, W441-W445
31. Wisniewska, M.; Karlberg, T.; Lehtio, L.; Johansson, I.; Kotenyova, T.; Moche, M.; Schuler, H. Crystal structures of the ATPase domains of four human Hsp70 isoforms: HSPA1L/Hsp70-hom, HSPA2/Hsp70-2, HSPA6/Hsp70B′, and HSPA5/BiP/GRP78 PLoS One 2010, 5 e8625
32. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res. 1997, 25, 3389-3402 (Pubitemid 27359211)
33. Schmitt, L.; Tampe, R. ATP-lipids-protein anchor and energy source in two dimensions J. Am. Chem. Soc. 1996, 118, 5532-5543 (Pubitemid 26233640)
34. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode Methods Enzymol. 1997, 276, 307-326 (Pubitemid 27085611)
35. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132 (Pubitemid 41742764)
36. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Refinement of macromolecular structures by the maximum-likelihood method Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240-255 (Pubitemid 27235885)
37. Potterton, E.; Briggs, P.; Turkenburg, M.; Dodson, E. A graphical user interface to the CCP4 program suite Acta Crystallogr., Sect. D: Biol. Crystallogr. 2003, 59, 1131-1137 (Pubitemid 36872348)